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  Home > JCE Print > Journal of Chemical Education > Issues > 2005  > October  >
Research: Science and Education
Using "Basic Principles" To Understand Complex Science: Nicotine Smoke Chemistry and Literature Analogies
Jeffrey I. Seeman
SaddlePoint Frontiers, Richmond, VA 23236
Cover
October 2005
Vol. 82 No. 10
p. 1577
Abstract
The Henderson–Hasselbalch equation calculates the equilibrium distribution of 50:50 for nicotine in its nonprotonated (free base form), relative to its monoprotonated form, at pH of 8 in dilute aqueous solution. This ratio has then been used in the literature to predict the effect of ammonia compounds in tobacco and in smoke on nicotine pyrolysis and smoke chemistry. Experiments demonstrate that neither the thermal chemistry of tobacco alkaloids nor the transfer of nicotine from tobacco to smoke can be explained by the position of the nonprotonated versus monoprotonated form equilibrium in aqueous extracts of tobacco. The high thermal stability of nicotine in air allows nicotine salts to be converted to nonprotonated nicotine and volatilize during heating prior to any substantial decomposition of the nicotine moiety. In contrast, cocaine hydrochloride is thermally unstable and will rapidly decompose upon heating; cocaine hydrochloride must first be converted to its nonprotonated form prior to heating and volatilization.
More Information
*  Citation
 Seeman, Jeffrey I. J. Chem. Educ. 2005 82 1577.
*  Keywords
 Acids / Bases; Analogies / Transfer; Applications of Chemistry; Calorimetry / Thermochemistry; Gases; General Public; Heterocycles; Misconceptions / Discrepant Events; Natural Products; Organic Chemistry; pH; Public Understanding / Outreach; Second-Year Undergraduate; Upper-Division Undergraduate
*  History
 Created:
Last Updated:		 August 30, 2005
September 8, 2005
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